CN101341165A - Enzymatic production of sucrose-6-ester, an intermediate for the manufacture of halo sugars - Google Patents
Enzymatic production of sucrose-6-ester, an intermediate for the manufacture of halo sugars Download PDFInfo
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- CN101341165A CN101341165A CNA2006800462216A CN200680046221A CN101341165A CN 101341165 A CN101341165 A CN 101341165A CN A2006800462216 A CNA2006800462216 A CN A2006800462216A CN 200680046221 A CN200680046221 A CN 200680046221A CN 101341165 A CN101341165 A CN 101341165A
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- C12P19/44—Preparation of O-glycosides, e.g. glucosides
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
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Abstract
A novel process is described for production of 6-acyl-sucrose comprising enzymatic acylation of sucrose by an esterifying agent including an organic acid in presence of a lipase or an esterase in a solvent in which the enzyme used is stable. Chlorinated sucrose, the high intensity sweetener trichlorogalactosucrose can be prepared by chlorination and deacylation of 6-acyl sucrose prepared by the process of this invention.
Description
Technical field
The present invention relates to the enzymatic production sucrose-6-ester, its be manufacturing comprise 1 '-6 '-two chloro-1 '-6 '-dideoxy-β-fructofuranose-4-chloro-4-deoxidation-galactopyranoside (TGS) with and the intermediate that uses during halogenation (chlorination) sucrose of precursor (TGS-6-ester).
Background technology
Art methods produces 4; 1 '; the strategy of 6 ' trichlorogalacto-sucrose (TGS) mainly comprises by using Vilsmeier-Haack reagent to come chlorinated sucrose-6-ester to form 6-ethanoyl-4; 1 '; 6 '-trichlorogalacto-sucrose, described Vilsmeier-Haack reagent source is in such as the different chlorination reagents of phosphorous oxychloride, oxalyl chloride, phosphorus pentachloride etc. with such as three grades of acid amides (tertiary amide) of dimethyl formamide (DMF) or N,N-DIMETHYLACETAMIDE.After the described chlorination reaction; the alkaline hydrated oxide neutralization reaction material that uses suitable calcium, sodium etc. is to pH 7.0～7.5; pH preferably further raise then so that 6-ethanoyl-4; 1 '; 6 '-trichlorogalacto-sucrose de-esterifying (deesterify)/deacetylation and form 4; 1 ', 6 ' trichlorogalacto-sucrose (TGS).
Sucrose-6-ester normally utilizes esterify sucrose and obtains, and is the precursor of TGS, and TGS is used for food and other zero calorie high intensity sweetener or taste modifier of using.Yet the esterification of sucrose must be carried out at 6 separately, and this is main challenge for its manufacturing, this be because the reactivity of the destination locations of this esterification more the competitive position of hyperergy (that is, 1 ' and 6 ') is lower than other.
In order to realize the esterification of regioselectivity, in the organic synthesis mode of making sucrose-6-ester, the whole bag of tricks has been described, it includes but not limited to that the adducts that is mediated by tin after the esterification generates and the direct esterification of sucrose in pyrimidine.Yet, by the method for organic synthesis, even process for selective also causes the generation of various by products and need relate to separating step with purifying sucrose-6-ester before chlorination.In the more controls that realize the special esterification of loci, need further improvement.
Summary of the invention
The invention discloses the method for enzymatic acylation; wherein; when sucrose in the presence of novel lipase or crosslinked lipase during with suitable acyl group or aryl esterifying agent (comprising organic acid) reaction; primary product is 6-acyl group-sucrose; this lipase be three grades of acid amides exist or not in the presence of free or immobilized form, or in what its The suitable solvent in office (wherein enzyme is stable).The reactant used according to esterification, the ester group that is incorporated on 6 of the sucrose moleculess can be alkyl, aryl, substituted alkyl or substituted aryl.Therefore the 6-acyl group-sucrose that obtains can be used to prepare halogenated sugars.
Prior art
Dordick etc. (1992) disclose in United States Patent (USP) no.5128248 4 '-and the 6-position at least one position on the sucrose or derivatives thereof is carried out the method for acidylate; wherein especially; when having microbial lipase, donor acyl ester and sucrose or derivatives thereof react in non-hydroxyl solvent.Described donor ester is straight chain alkanoic acid or benzoic reactive ester.
Bornemann etc. (1992) disclose the method that the preparation part is removed the sucrose acylate of acidylate in United States Patent (USP) no.5141860; this sucrose acylate has at least at 2-in each ring; ethanoyl and at least one free hydroxyl group at 3-and 3 '-place, position; wherein sucrose decoyl ester (sucroseoctaacylate) is with the combined treatment of enzyme or enzyme; the combination of this enzyme or enzyme can be in the aqueous medium that is buffered to pH 5-7 (comprise water and up to 50% organic solvent) the hydrolysis of at least one acyl group on each ring of the described sucrose decoyl of catalysis ester; and separate the part that generates and remove the sucrose acylate of acidylate, described enzyme is selected from by steapsin; the yeast esterase; fungi; α-Dian Fenmei; subtilisin; in the group that Semialkaline Protease and alpha-galactosidase are formed.
Embodiment
The enzymatic route is significantly special to its end product.They also are unusual substrate specificities.
The invention describes the novel method that utilizes enzyme to produce sucrose-6-ester.It has been described sucrose enzymatic esterification efficiently and optionally.Utilize novel lipase or crosslinked esterase to carry out regioselective reaction, this enzyme be or free or immobilization form or what its The suitable solvent in office (wherein enzyme is stable) when three grades of acid amides exist or do not exist in.The reactant used according to esterification, the ester group that is incorporated on 6 of the sucrose moleculess can be alkyl, aryl, substituted alkyl or substituted aryl.Therefore the 6-acyl group-sucrose that obtains can be used to prepare halogenated sugars, for example as the TGS of intense sweetener.
Employed enzyme can be esterase, lipase etc.These enzymes can be fixed among the synthetic polymeric support or on, this polymeric support is such as but not limited to polyacrylic acid, or polystyrene or polyacrylamide, based on the upholder of nylon; Perhaps as the semisynthetic or natural organic upholder based on polysaccharide, this polysaccharide is such as but not limited to Mierocrystalline cellulose, starch, dextran, agarose, chitosan, chitin etc.; Perhaps inorganic upholder, for example based on those of carbon, silicon, zirconium white, aluminum oxide, zirconium phosphate, or the like.
The source of lipase can be to come from animal, plant or microorganism, more preferably come from microorganism or bacterium, for example Bacillus thermocatenulatusis, Pseudomonas aeruginosa etc., fungi, for example Penicillium Roquefortii, Asperigillus niger, Asperigillus oryzae, Rhizopusniveus, Candida rugosa, Rhizomucor miheii, Candida antartctica etc. or equivalent.
This strategy has improved the productive rate and the purity of sucrose-6-ester on effect, this sucrose-6-ester itself or be used for chlorinating step after desolvating removing, and with the preparation chlorinated sucrose derivative, this improves the purity and the productive rate of the chlorinated sucrose of being produced again.
In the present invention, the Enzymatic transformation of sucrose becomes cane sugar-6-acetic ester to consist essentially of to use sucrose and acetate or suitable organic acid or suitable acyl group or aryl esterification to study to reactant with the sucrose-6-ester of direct production as primary product.
Following inventive method is the efficient region selective reaction, wherein utilizes novel separation lipase to carry out optionally sucrose esterification at 6 specially first.
In the methods of the invention, by being handled, sucrose dissolved carries out this reaction in exsiccant DMF and with lipase.Sucrose concentration in the DMF solution from 1: 1 to 1: 10w/v changes.Acetate is used as acylating agent and is introduced directly in the reaction mixture.The aromatic acid of lipid acid, aromatic acid or replacement that can use any other lipid acid, replacement is to generate sucrose-6-ester separately.Temperature between the reaction period can be the arbitrary value in 15 ℃～60 ℃.Enzymatic esterification 1 hour～finish more than 16 hours, and follow the production of by-products (if having words) of negligible quantity.When suitable maintenance reaction conditions, sucrose is fairly good and special to 6 to the conversion of sucrose-6-ester.This enzyme can use with the free form such as powder or liquid, also can be the immobilization form.
Enzyme is recovered when using with the immobilization form.Immobilized enzyme can be packed in the post and with set flow velocity by described reactant to react.Perhaps, after in reactor, reacting and react, can reclaim enzyme by from reaction mass, enzyme being filtered out with immobilized enzyme.
Therefore the sucrose-6-ester that obtains is pure basically and is easy to separate and carry out chlorination and produce halogenated sugars.
That describe below is embodiment, and it has illustrated mode of operation of the present invention and the scope that do not limit the present invention in any way.The scope of the ratio of reactant, employed reactant, the reaction conditions of description only is that scope illustrative and of the present invention extends to its similar reactant, reaction conditions and similarly general character reaction.Usually, the conspicuous any equivalent substitution of chlorinated sucrose production field technician is included in the scope of this specification sheets.Unless do not allow in the literary composition, mentioned odd number is understood to include its plural form, and comprise all equivalent substitutions that comprise by this statement, that is, use " chlorinated sucrose " comprise in all chlorinated sucrose compound every kind with and composition thereof or in associated viscera, can realize the alternate chlorinated sucrose compound of identical function.Mention that " a kind of organic solvent " that be used for solution comprises that one or more organic solvents use continuously, or its combination uses as mixture, maybe can carry out any in some the substituting with claim, specification sheets is described or embodiment is illustrated identical function.In this manual, sucrose-6-ester and 6-acyl group-sucrose exchange use for all functions purpose as equivalent.
Embodiment 1, the sucrose enzymatic acetylization reaction in DMF
Will from the lipase of Asperigillus oryzae on polystyrene bead immobilization and with glutaraldehyde cross-linking with being fixed lipase.200g sucrose in 80 ℃ of DMF that are dissolved in 800ml and be cooled to room temperature, is added the described immobilized lipase of 34g and keeps stirring in reaction flask.Keeping temperature is 30 ℃.In reaction flask, drip 13.5g acetate and continue stirring.Continue stirring and monitor acetylization reaction with TLC and HPLC.
In 3 hours, finished 70% acetylize, filtering reaction inclusion (reaction content) and water flushing enzyme and recovery.
HPLC confirms to generate 70% cane sugar-6-acetic ester, and no coupling product generates.
Embodiment 2, the sucrose enzymatic acetylization reaction in primary isoamyl alcohol
20g sucrose is partially dissolved in the 400ml primary isoamyl alcohol and is cooled to room temperature in 80 ℃.In reaction flask, add 34g as method preparation as described in the embodiment 1 from the immobilized lipase of Asperigillus oryzae and keep stirring.Keeping temperature is 30 ℃.In reaction flask, drip 3.5g acetate and continue stirring.Continue stirring and monitor acetylization reaction with TLC and HPLC.
Finished 70% acetylize and filtering reaction inclusion in 3 hours, water flushing enzyme also reclaims.HPLC confirms to generate 70% cane sugar-6-acetic ester, and no coupling product generates.
Embodiment 3, utilize phthalic anhydride with sucrose enzymatic acylation in DMF
With 10g sucrose in 50 ℃ of DMF that are partially dissolved in 100ml and be cooled to 25 ℃.Adding 26g separates from the lipase of Pseudomonas sp. and fully stirring.Temperature rises to 50 ℃ once more.The phthalic anhydride and the sustained reaction 6.0h that add 0.59ml.With TLC and HPLC monitoring acylation reaction.
In 6 hours, realize benzoylation, and no coupling product generates up to 48%.
Embodiment 4, utilize lauric acid with sucrose enzymatic acylation in DMSO
With 10g sucrose in 60 ℃ of DMSO (methyl-sulphoxide) that are dissolved in 100ml and be cooled to 25 ℃.Adding 26g separates from the lipase of Rhizopus sp. and fully stirring.Temperature rises to 50 ℃ once more.Add 11.69g lauric acid and sustained reaction 8.0h.With TLC and HPLC monitoring acylation reaction.
The HPLC affirmation realized the acidylate up to 42% in 8 hours, and no coupling product generates.
Embodiment 5, utilize the p-nitrobenzoic acid with sucrose enzymatic acylation in DMSO
With 10g sucrose in 60 ℃ of DMSO that are dissolved in 100ml and remain on 35 ℃.Adding 26g separates from the lipase of pseudomonas sp. and fully stirring.Temperature rises to 60 ℃ once more.The p-nitrobenzoic acid and the sustained reaction 8.0h that add 4.89g.With TLC and the reaction of HPLC monitoring benzoylation.
The HPLC affirmation realized the benzoylation up to 32% in 8 hours, and no coupling product generates.
Embodiment 6, enzymatic acetylize and chlorination reaction are with preparation TGS
In an experiment, with 200g sucrose in 80 ℃ of DMF that are dissolved in 2000ml and be cooled to room temperature.In reaction flask, add 34g as method preparation as described in the embodiment 1 from the immobilized lipase of Asperigillusoryzae and keep stirring.Keeping temperature is 50 ℃.In reaction flask, drip the 13.8ml diacetyl oxide and continue stirring.Continue stirring and monitor acetylization reaction with TLC and HPLC.
In 6 hours, finished acetylize, filtering reaction inclusion and water flushing enzyme and recovery up to 68%.Then DMF solution is used for chlorination.
PCl with 432g
5In 35 ℃ of DMF that are added to 2L and allow to form VilsmeierHaack reagent.POCl by this reaction generation
3Form the 2nd Vilsmeier with available DMF in the reaction mass, and fully stir this reaction mass 60min.Then this reaction mass is cooled to 0 ℃ and the under agitation slow 6-acyl sucrose that adds among the DMF that obtains by enzymatic reaction.After adding the 6-acyl sucrose, this reaction mass is heated to 35 ℃ and maintenance stirring 60min.Reacting by heating material to 85 ℃ keeps 60min then, is heated to 100 ℃ once more, keeps 6h, further is heated to 114 ℃ and keep 1.5h then, is cooled to 65 ℃ then.
Utilize calcium hydroxide pulp-water neutralization reactant material to pH 7.0 then, filter then.Then, filtrate is extracted in the ethyl acetate of 1: 3 times of v/v, and is concentrated into 50% of its initial volume.Use the saturated nacl aqueous solution of 1: 0.1 times of v/v to wash this extract then.Repeat this sodium-chlor flushing 12 times, and the DMF content in the ethyl acetate extract is decreased to＜0.1%.Then, thoroughly remove ethyl acetate, and with these slurries at the enterprising circumstances in which people get things ready for a trip spectrum analysis of silication silica gel.The moving phase of using is the damping fluid of pH 10.5～11.0.
Collection uses sodium hydroxide solution to regulate pH to 9.0 by the pure fraction that chromatogram purification obtains then.Allow to finish deacetylation and confirm by TLC.
Behind the deacetylation, concentrate this cut by the molecular separation of utilizing the RO film.Enriched material after RO concentrated is extracted in the ethyl acetate of 1: 3.5 times of v/v and separates each layer.Ethyl acetate extract is concentrated into maximum value, and the crystal that is obtained dissolves in methyl alcohol again.Filter methanol solution then to remove any impurity and it is concentrated and crystallization.
HPLC measures, and the purity of acquisition is 98.5%, and the overall yield that is obtained by the input of 6-acyl sucrose is 35%.
Embodiment 7, utilize the enzymatic phthalation reaction of esterase in the t-butanols
With 25g sucrose in 60 ℃ of t-butanols that are partially dissolved in 100ml and be cooled to 25 ℃.Adding 45g separates from the lipase of candida sp. and fully stirring.Temperature is risen to 60 ℃ once more.Add 4.89g phthalic acid and sustained reaction 16.0h.With TLC and HPLC monitoring phthalation reaction.
The HPLC affirmation realized the phthalation up to 26% in 16 hours, and no coupling product generates.
Embodiment 8, utilization are packaged in the enzymatic acylation reaction of the immobilized lipase in the post
With 25g sucrose in 80 ℃ of DMF that are partially dissolved in 100ml and be cooled to 25 ℃.With the immobilized lipase from Pseudomonas sp. of 15g on the polystyrene upholder glass column of packing into.The inlet of post is connected to sucrose solution among the DMF by peristaltic pump.Outlet also is connected to sucrose solution.At 25 ℃ of lasting stirred solutions.4.0ml acetate joined in the sucrose solution and pump into glass column with the flow velocity of 20ml/h by peristaltic pump.Continue recirculation 12h.Periodically monitor acetylization reaction with TLC.
The HPLC affirmation realized the acetylize up to 59% in 12 hours, and no coupling product generates.
Claims (6)
1, a kind of main on the 6-position acidylate sucrose to prepare the method for 6-acyl group-sucrose, wherein, use enzyme, when the organic acid that comprises straight chain alkanoic acid or aryl carboxylic acid, or acylating agent and sucrose is when reacting in solvent, this enzyme can be on 6 of sucrose molecules the catalytic selectivity acidylate; Described solvent is the stable therein solvent of described enzyme.
2, the described method of claim 1 is characterized in that,
A, the described organic acid of straight chain alkanoic acid or aryl carboxylic acid that comprises further comprise acetate, propionic acid, butyric acid, acid, phenylformic acid, phthalic acid etc.,
B, described acylating agent comprise diacetyl oxide, propionic anhydride, lauric anhydride, butyryl oxide, benzoyl oxide, phthalate anhydride etc.,
C, described enzyme comprise lipase or esterase, and it is solvable or the immobilization form, and come from animal, plant or microorganism,
D, described enzyme are that stable described solvent comprises dimethyl formamide, primary isoamyl alcohol, octanol, hexane, hexanaphthene, toluene, t-butanols, dimethyl sulfoxide (DMSO) etc. therein.
3, claim 1 or 2 described methods is characterized in that, comprise the steps:
A, with sucrose dissolved in solvent to produce solution, preferably in anhydrous solvent and described solvent be the stable therein solvent of described enzyme,
B, in described solution, add lipase or esterase,
Add acetate or another kind of organic acid or acylating agent in c, the reaction mixture in abovementioned steps,
D, allow to be reflected under the temperature that promotes the enzyme effect and carry out, preferred 15～60 ℃, continue to be enough to obtain sucrose for some time, preferred about 1～16h to the actual maximum conversion of 6-ethanoyl-sucrose.
4, claim 1 or 2 described methods; it is characterized in that; the acidylate of sucrose comprises reactor; wherein; at a certain temperature; being enough to make most of sucrose acidylates is in for some time of 6-acyl group-sucrose, and described enzyme is in contact with one another with the circulate soln that contains sucrose and organic acid or acylating agent in reactor with the immobilization form.
5, the described method of claim 4 is characterized in that,
A, sucrose is in certain temperature, is dissolved in the solvent under preferred about 80 ℃, and preferably be partially dissolved in DMF, and be cooled to a temperature, 25 ℃ of preferably approximatelies,
B, preferred lipase that will fixed extracts from pseudomonas sp on preferred polystyrene upholder be encapsulated into glass column,
C, with the inlet of this post by pump, preferred peristaltic pump is connected to the sucrose solution among the DMF,
D, the outlet of this post is connected to the described sucrose solution of indication among a of this claim,
E, preferably continue to stir these solution at about 25 ℃,
F, with organic acid, preferred acetate add sucrose solution and by peristaltic pump with certain flow rate, preferably about 20ml/h pumps in the glass column, continue to carry out recirculation for some time, preferably approximately 12h so that the sucrose of considerable part is transformed into 6-acyl group-sucrose, and
6-acyl group-sucrose that therefore g, selectable use obtain is with the preparation chlorinated sucrose.
6, the described method of claim 1 is characterized in that, the reaction solution stream of the resulting 6-of containing acyl group-sucrose is carried out chlorination and deacetylation, to produce chlorinated sucrose, comprises intense sweetener 4,1 ', 6 ' trichlorogalacto-sucrose (TGS).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1522/MUM/2005 | 2005-12-09 | ||
| IN1522MU2005 | 2005-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101341165A true CN101341165A (en) | 2009-01-07 |
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ID=38123300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2006800462216A Pending CN101341165A (en) | 2005-12-09 | 2006-11-28 | Enzymatic production of sucrose-6-ester, an intermediate for the manufacture of halo sugars |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20100216195A1 (en) |
| CN (1) | CN101341165A (en) |
| CA (1) | CA2632659A1 (en) |
| GB (1) | GB2447170A (en) |
| WO (1) | WO2007066356A2 (en) |
| ZA (1) | ZA200804930B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102161683A (en) * | 2011-02-24 | 2011-08-24 | 浙江工业大学 | Method for synthesizing sucrose-6-palmitate by using lipase through catalytic selectivity |
| CN103805653A (en) * | 2014-01-15 | 2014-05-21 | 盐城捷康三氯蔗糖制造有限公司 | Method for ultrasonic-assisted enzymatic synthesis of sucrose-6-ester suitable for industrial production |
| CN106188170A (en) * | 2016-07-02 | 2016-12-07 | 安徽广信农化股份有限公司 | A kind of method that enzymology combination method prepares sucrose 6 acetas |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2013005560A (en) | 2010-11-23 | 2013-08-26 | Lexington Pharmaceuticals Lab Llc | Low temperature chlorination of carbohydrates. |
| CN102181494A (en) * | 2011-03-21 | 2011-09-14 | 盐城捷康三氯蔗糖制造有限公司 | Synthesis of sucrose-6-fatty acid ester through selective catalysis of immobilized aspergillus oryzae lipase |
| SG2013049648A (en) | 2011-10-14 | 2014-12-30 | Lexington Pharmaceuticals Lab Llc | Chlorination of carbohydrates and carbohydrate derivatives |
| WO2017189778A1 (en) * | 2016-04-26 | 2017-11-02 | Chromocell Corporation | Methods, compounds, and compositions, for modulating sweet taste |
| WO2020200879A1 (en) * | 2019-04-04 | 2020-10-08 | Universiteit Gent | A continuous flow process for the preparation of sugar esters |
| CN111763703B (en) * | 2020-07-02 | 2022-07-19 | 浙江工业大学 | Method for synthesizing sucrose-6-ethyl ester by enzyme method in organic solvent |
| WO2022151024A1 (en) * | 2021-01-13 | 2022-07-21 | 安徽金禾实业股份有限公司 | Immobilization method of liquid lipase and preparation method of sucrose-6-acetate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8822673D0 (en) * | 1988-09-27 | 1988-11-02 | Tate & Lyle Plc | Selective acylation of sugars |
| GB8822674D0 (en) * | 1988-09-27 | 1988-11-02 | Tate & Lyle Plc | Preparation of acylated sucrose derivatives |
-
2006
- 2006-11-28 US US12/086,175 patent/US20100216195A1/en not_active Abandoned
- 2006-11-28 CN CNA2006800462216A patent/CN101341165A/en active Pending
- 2006-11-28 GB GB0810490A patent/GB2447170A/en not_active Withdrawn
- 2006-11-28 CA CA002632659A patent/CA2632659A1/en not_active Abandoned
- 2006-11-28 WO PCT/IN2006/000478 patent/WO2007066356A2/en active Application Filing
-
2008
- 2008-06-05 ZA ZA200804930A patent/ZA200804930B/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102161683A (en) * | 2011-02-24 | 2011-08-24 | 浙江工业大学 | Method for synthesizing sucrose-6-palmitate by using lipase through catalytic selectivity |
| CN103805653A (en) * | 2014-01-15 | 2014-05-21 | 盐城捷康三氯蔗糖制造有限公司 | Method for ultrasonic-assisted enzymatic synthesis of sucrose-6-ester suitable for industrial production |
| CN103805653B (en) * | 2014-01-15 | 2015-07-29 | 盐城捷康三氯蔗糖制造有限公司 | Be applicable to the method for industrial ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester |
| CN106188170A (en) * | 2016-07-02 | 2016-12-07 | 安徽广信农化股份有限公司 | A kind of method that enzymology combination method prepares sucrose 6 acetas |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2447170A (en) | 2008-09-03 |
| WO2007066356A2 (en) | 2007-06-14 |
| US20100216195A1 (en) | 2010-08-26 |
| ZA200804930B (en) | 2009-12-30 |
| WO2007066356A3 (en) | 2007-11-01 |
| GB0810490D0 (en) | 2008-07-09 |
| CA2632659A1 (en) | 2007-06-14 |
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